1621673-53-7 Usage
Description
4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide, also known as KY-226 (CAS 1621673-53-7), is a selective allosteric protein tyrosine phosphatase 1B (PTP1B) inhibitor with an IC50 of 250 nM. It is characterized by its lack of activity at PPARγ and has demonstrated significant potential in various applications due to its unique properties and mechanisms of action.
Uses
Used in Pharmaceutical Industry:
4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide is used as an anti-diabetic agent for enhancing insulin signaling and improving plasma glucose, triglyceride, and A1c levels without causing weight gain in db/db mice. Its anti-diabetic effects are suggested to occur via enhancements in insulin signaling and anti-obesity effects via leptin signaling enhancements.
Used in Neuroprotection:
In the field of neuroscience and neurology, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide is used as a neuroprotective agent for protecting neurons from cerebral ischemia. This protective effect is mediated by the restoration of tight junction proteins via activation of the Akt/FoxO1 pathway.
References
1) Morashita (2017),?Novel Non-carboxylate Benzoylsulfonamide-Based Protein Tyrosine Phosphatase 1B Inhibitor with Non-competitive Actions;?Chem.Pharm.Bull.?65?1144
2) Ito?et al.?(2018),?Therapeutic effects of the allosteric protein tyrosine phosphatase 1B inhibitor KY-226 on experimental diabetes and obesity via enhancements in insulin and leptin signaling in mice;?J.Pharmacol.Sci?137?38
3) Sun?et al.?(2018),?Neuroprotective effects of protein tyrosine phosphatase 1B on cerebral ischemia/reperfusion in mice;?Brain Res.?1694?1
4) Sun?et al.?(2019),?KY-226 Protects Blood-brain Barrier Function Through the Akt/FoxO1 Signaling Pathway on Brain Ischemia;?Neuroscience?399?89
Check Digit Verification of cas no
The CAS Registry Mumber 1621673-53-7 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,6,2,1,6,7 and 3 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1621673-53:
(9*1)+(8*6)+(7*2)+(6*1)+(5*6)+(4*7)+(3*3)+(2*5)+(1*3)=157
157 % 10 = 7
So 1621673-53-7 is a valid CAS Registry Number.
1621673-53-7Relevant articles and documents
Novel non-carboxylate benzoylsulfonamide-based protein tyrosine phosphatase 1B inhibitors with non-competitive actions
Morishita, Ko,Shoji, Yoshimichi,Tanaka, Shunkichi,Fukui, Masaki,Ito, Yuma,Kitao, Tatsuya,Ozawa, Shin-Ichiro,Hirono, Shuichi,Shirahase, Hiroaki
, p. 1144 - 1160 (2017)
A novel series of benzoylsulfonamide derivatives were synthesized and biologically evaluated. Among them, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzamide (compound 18K) was identified as a protein tyrosine phosphatase 1B (PTP1B) inhibitor with potent and selective inhibitory activity against PTP1B (IC50 = 0.25 μM). Compound 18K functioned as a non-competitive inhibitor and bound to the allosteric site of PTP1B. It also showed high oral absorption in mice (the maximum drug concentration (Cmax) = 45.5 μM at 30 mg/kg), rats (Cmax = 53.6 μM at 30 mg/kg), and beagles (Cmax = 37.8 μM at 10 mg/kg), and significantly reduced plasma glucose levels at 30 mg/kg/d (per os (p.o.)) for one week with no side effects in db/db mice. In conclusion, the substituted benzoylsulfonamide was shown to be a novel scaffold of a noncompetitive and allosteric PTP1B inhibitor, and compound 18K has potential as an efficacious and safe antidiabetic drug as well as a useful tool for investigations of the physiological and pathophysiological effects of allosteric PTP1B inhibition.
